There is an absence of theoretically guided research upon which to develop gender specific interventions for women who engage in risk behaviors, such as illicit substance use, that increase the probability of involvement in the criminal justice system. Research investigating such behaviors has primarily generated descriptive finding and most of the studies have been based on samples in which all respondents engage in high levels of risky behavior. The result is that the mechanism(s) by which some women come to engage in high risk behaviors while other do not has not been well elucidated. This research utilizes respondents, and the data they have provided, as participants in a longitudinal study of young women who gave birth as adolescents - some of whom engage in high levels of risky behavior and others that do not. To address gaps in the literature, this project will develop, refine, and test two hypothesized models: (1) the relationship between trauma, adult attachment, and substance use and (2) an extension of the first, assessing the relationship between trauma, attachment, risky behavior, and incarceration. Finally, social context of substance use and lawbreaking will be investigated, with findings organized around the theoretical models to be tested.